CH89636A - Process for the preparation of the Bromdiäthylacetylurethans of p-acetylaminophenol. - Google Patents
Process for the preparation of the Bromdiäthylacetylurethans of p-acetylaminophenol.Info
- Publication number
- CH89636A CH89636A CH89636DA CH89636A CH 89636 A CH89636 A CH 89636A CH 89636D A CH89636D A CH 89636DA CH 89636 A CH89636 A CH 89636A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acetylaminophenol
- bromdiäthylacetylurethans
- weight
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 230000001754 anti-pyretic effect Effects 0.000 claims description 2
- 239000002221 antipyretic Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000000147 hypnotic effect Effects 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 claims description 2
- 230000001624 sedative effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- CLLOFODTUXGHHT-UHFFFAOYSA-N ethyl n-acetylcarbamate Chemical compound CCOC(=O)NC(C)=O CLLOFODTUXGHHT-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- SXLHPBDGZHWKSX-UHFFFAOYSA-N 1-(5-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC(N)=CC=C1O SXLHPBDGZHWKSX-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 p-acetylaminophenol urethane Chemical compound 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung des Bromdiäthylacetyluretlians des p-Acetylaiiiii)oplieitols. Es wurde gefunden, dass man das bisher unbekannte Bromdiäthylacetyltirethan des p-Acetylaminopheiiols der Formel:
Cy H.5 <B><I>>C</I> *</B> Br <B>- CO -</B> NH <B>- CO - 0 -</B> C@114 -NH*C0eCH:i C2H5 das ein therapeutisch wertvoller, geschmack loser Körper ist, dadurch erhalten kam), dass man Acety#-p-aminophenoltirethan mit (f-Brom- diäthylessigsätit-ehalogeriid behandelt, wobei die gebildete Halogenwasserstoffsäure nicht in das Endprodukt eintritt.
Der neue Körper kristallisiert aus Alkohol in schmalen weissen Blättchen, die b#-i 144<B>0</B> schmelzen. Sie sind leicht löslich in Alkohol und Aceton, schwer löslich in Benzol, Äther und Wasser. Er besitzt neben guten anti- pyretisehen und antineuralgischen auch deut liche sedative und hypnotische Wirkungen. <I>Beispiel:</I> Zu einer Mischung von 194 Gewichtsteilen p-Acetylaminophenolurethan und 121 Ge wichtsteilen Dimethylanilin werden unter Rühren langsam<B>271</B> Gewichtsteile Brom- diätliylacetyleliloi-id zugefügt.
Die Masse er wärmt sich und wird zur Beendigung der Reaktion noch kurze Zeit auf<B>1 0 "</B> gebracht. Darauf wird dieselbe init <B>500</B> Gewichtsteilen Aceton durchgerührt, abgesaugt und das <B>so</B> erhaltene Bromdiäthyl.teetyl(irethan des p-Ace- tylaminophenols durch eine Behandlung init, etwas Äther vorgereinigt und aus Alkohol <B>k3</B> umkristallisiert.
Das in diesem Beispiel als Ausgangs- niaterial beiititzteNi-Acetylaiiiitioplienolui,ethait wird zum Beispiel durch Verschmelzen von <B>167</B> Gewichtsteilen Gruajakolurethan mit<B>158</B> Gewielitsteilen p-Acetylamiiiophetiol im Ölbad bei<B>150 1</B> gewonnen, wobei Guajakol ab- destilliert.
Process for the preparation of the Bromdiäthylacetyluretlians des p-Acetylaiiiii) oplieitols. It has been found that the previously unknown Bromdiäthylacetyltirethan des p-Acetylaminopheiiols of the formula:
Cy H.5 <B> <I>> C </I> * </B> Br <B> - CO - </B> NH <B> - CO - 0 - </B> C @ 114 -NH * C0eCH: i C2H5 which is a therapeutically valuable, tasteless body, was obtained by treating acetyl-p-aminophenol tirethane with (f-bromo diethyl acetic acid ehalogenide, whereby the hydrohalic acid formed does not enter the end product.
The new body crystallizes from alcohol in narrow white flakes that melt b # -i 144 <B> 0 </B>. They are easily soluble in alcohol and acetone, poorly soluble in benzene, ether and water. In addition to good antipyretic and antineuralgic effects, it also has clear sedative and hypnotic effects. <I> Example: </I> To a mixture of 194 parts by weight of p-acetylaminophenol urethane and 121 parts by weight of dimethylaniline are slowly added <B> 271 </B> parts by weight of bromodietliylacetyleliloid with stirring.
The mass warms up and is brought to <B> 10 "for a short time to end the reaction. The same is then stirred in <B> 500 </B> parts by weight of acetone, suctioned off, and that way Bromdiäthyl.teetyl (irethane of p-acetylaminophenol obtained by a treatment with a little ether pre-purified and recrystallized from alcohol <B> k3 </B>.
The Ni-Acetylaiiiitioplienolui, ethait used as the starting material in this example is made, for example, by fusing <B> 167 </B> parts by weight of Gruajakolurethane with <B> 158 </B> parts by weight of p-Acetylamiiiophetiol in an oil bath at <B> 150 1 </B> won, with guaiacol distilled off.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE89636X | 1915-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH89636A true CH89636A (en) | 1921-06-01 |
Family
ID=5642847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH89636D CH89636A (en) | 1915-12-27 | 1916-12-27 | Process for the preparation of the Bromdiäthylacetylurethans of p-acetylaminophenol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH89636A (en) |
-
1916
- 1916-12-27 CH CH89636D patent/CH89636A/en unknown
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